1.0 2010-04-08 22:04:26 UTC 2025-11-18 22:16:06 UTC FDB000095 ent-Gallocatechin 3-gallate Ent-gallocatechin 3-gallate, also known as (-)-gallocatechol gallic acid, is a member of the class of compounds known as catechin gallates. Catechin gallates are organic compounds containing a gallate moiety glycosidically linked to a catechin. Ent-gallocatechin 3-gallate is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Ent-gallocatechin 3-gallate can be found in tea, which makes ent-gallocatechin 3-gallate a potential biomarker for the consumption of this food product. (-)-Gallocatechin 3-O-gallate 3,3',4',5,5',7-Hexahydroxyflavan; (2S,3R)-form, 3-O-(3,4,5-Trihydroxybenzoyl) ent-Gallocatechin 3-gallate L-Gallocatechin 3-gallate C22H18O11 458.3717 458.084911418 (2S,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate gallocatechin gallate 68-22-4 OC1=CC2=C(C[C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@@H](O2)C2=CC(O)=C(O)C(O)=C2)C(O)=C1 InChI=1S/C22H18O11/c23-10-5-12(24)11-7-18(33-22(31)9-3-15(27)20(30)16(28)4-9)21(32-17(11)6-10)8-1-13(25)19(29)14(26)2-8/h1-6,18,21,23-30H,7H2/t18-,21+/m1/s1 WMBWREPUVVBILR-NQIIRXRSSA-N belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Flavonoid O-glycosides Organic compounds Phenylpropanoids and polyketides Flavonoids Flavonoid glycosides Aromatic heteromonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids 2'-Hydroxy-dihydrochalcones Acetals Alkyl-phenylketones Aryl alkyl ketones Benzoyl derivatives Butyrophenones Catechols Cinnamylphenols Hexoses Hydrocarbon derivatives O-glycosyl compounds Organic oxides Oxacyclic compounds Oxanes Phenol ethers Phenolic glycosides Phenoxy compounds Polyols Primary alcohols Resorcinols Secondary alcohols Vinylogous acids 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 2'-hydroxy-dihydrochalcone Acetal Alcohol Alkyl-phenylketone Aromatic heteromonocyclic compound Aryl alkyl ketone Aryl ketone Benzenoid Benzoyl Butyrophenone Catechol Cinnamylphenol Flavonoid o-glycoside Glycosyl compound Hexose monosaccharide Hydrocarbon derivative Ketone Linear 1,3-diarylpropanoid Monocyclic benzene moiety Monosaccharide O-glycosyl compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxane Phenol Phenol ether Phenolic glycoside Phenoxy compound Phenylketone Polyol Primary alcohol Resorcinol Secondary alcohol Vinylogous acid logp 2.38 ALOGPS logs -3.80 ALOGPS solubility 7.28e-02 g/l ALOGPS logp 3.08 ChemAxon pka_strongest_acidic 7.99 ChemAxon pka_strongest_basic -5.4 ChemAxon iupac (2S,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate ChemAxon average_mass 458.3717 ChemAxon mono_mass 458.084911418 ChemAxon smiles OC1=CC2=C(C[C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@@H](O2)C2=CC(O)=C(O)C(O)=C2)C(O)=C1 ChemAxon formula C22H18O11 ChemAxon inchi InChI=1S/C22H18O11/c23-10-5-12(24)11-7-18(33-22(31)9-3-15(27)20(30)16(28)4-9)21(32-17(11)6-10)8-1-13(25)19(29)14(26)2-8/h1-6,18,21,23-30H,7H2/t18-,21+/m1/s1 ChemAxon inchikey WMBWREPUVVBILR-NQIIRXRSSA-N ChemAxon polar_surface_area 197.37 ChemAxon refractivity 111.75 ChemAxon polarizability 42.81 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 10 ChemAxon donor_count 8 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 75327 Specdb::MsMs 75328 Specdb::MsMs 75329 Specdb::MsMs 134949 Specdb::MsMs 134950 Specdb::MsMs 134951 Specdb::MsMs 1479313 Specdb::MsMs 1479420 Specdb::MsMs 3596626 Specdb::MsMs 3596627 Specdb::MsMs 3596628 Specdb::MsMs 3596629 Specdb::MsMs 3596630 Specdb::MsMs 3596631 Black tea Type 1 4090.0 4090.0 4090.0 mg/100 g Green tea Type 1 4090.0 4090.0 4090.0 mg/100 g Herbal tea Type 1 4090.0 4090.0 4090.0 mg/100 g Red tea Type 1 4090.0 4090.0 4090.0 mg/100 g Tea Type 1 specific Camellia sinensis 4442 4090.0 4090.0 4090.0 mg/100 g